| Year | Winner | Book | Publisher |
|---|---|---|---|
| 2009 | Mark Leiren-Young | Never Shoot a Stampede Queen | Heritage House Publishing |
| 2008 | Terry Fallis | The Best Laid Plans | iUniverse, Inc. |
| 2007 | Stuart McLean | Secrets from the Vinyl Cafe | Viking |
| 2006 | Arthur Black | Pitch Black | Harbour Publishing |
| 2005 | Will Ferguson | Beauty Tips from Moose Jaw | Alfred A. Knopf, Canada |
| 2004 | Ian Ferguson | Village of Small Houses | Douglas & McIntyre Ltd. |
| 2003 | Dan Needles | With Axe and Flask - A History of Persephone Township | McFarlane Walter & Ross |
| 2002 | Will Ferguson | Generica (now renamed Happiness) | Penguin |
| 2001 | Stuart McLean | Vinyl Cafe Unplugged | Penguin Books of Canada |
| 2000 | Arthur Black | Black Tie and Tales | Stoddart Press |